Allyl bromide → Ethyl 2-allylhexadecanoate

HRID 358730Notes

Reaction equation

HRID 358730 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(NC(C)C)(C)C.[C:13]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(Br)C=C>O1CCCC1>[CH2:3]([CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:13]([O:30][CH2:31][CH3:32])=[O:29])[CH:2]=[CH2:1]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 12366Ethyl palmitateHCID 178418339Butyllithium

Product 1

HCID 14785825Ethyl 2-allylhexadecanoateYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of n-butyl lithium (hexane, 0.048 mol) in 120 mL of anhydrous tetrahydrofuran at 0° C. and under argon atmosphere, diisopropylamine was added (6.8 mL, 0.048 mol). Afterwards, ethyl hexadecanoate (11.3 g, 0.04 mol) in tetrahydrofuran (15 mL) was added dropwise and the homogeneous solution was stirred for 1 h at the same temperature. Next, allyl bromide (4.0 mL, 0.048 mol) was added and the resulting mixture was stirred at room temperature for 12 h. The mixture was poured on water, extracted with ethyl acetate, dried over anhydrous sodium sulfate and the solvent evaporated to afford 11.9 g of an oil. The product was chromatographed (silica gel, hexane: ethyl acetate, 3%) to afford 8.7 g of a colorless oil (67% yield).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 12 h
  2. additionThe mixture was poured on water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-7b9892d5fac7411996e6686b14abe93f
Source dataset
uspto-grants-1991_03
Patent number
US04997843

Reaction notes

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